Triethylamine → 7-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889103Notes

Reaction equation

HRID 1889103 reaction equation
[S:1]1[C:5]([C:6]2[N:10]3[CH2:11][CH2:12][NH:13][CH2:14][C:9]3=[N:8][N:7]=2)=[N:4][CH:3]=[N:2]1.C(N(CC)CC)C.[Cl:22][C:23]1[C:31]([F:32])=[C:30]([Cl:33])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C([O-])(O)=O.[Na+]>ClCCl.CO.C(OCC)(=O)C>[Cl:22][C:23]1[C:31]([F:32])=[C:30]([Cl:33])[CH:29]=[CH:28][C:24]=1[C:25]([N:13]1[CH2:12][CH2:11][N:10]2[C:6]([C:5]3[S:1][N:2]=[CH:3][N:4]=3)=[N:7][N:8]=[C:9]2[CH2:14]1)=[O:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 665987953-(1,2,4-Thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazineHCID 866667452,4-Dichloro-3-fluorobenzoyl chloride

Product 1

HCID 665992327-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (I115) (30 mg, 0.144 mmol) and triethylamine (0.030 mL, 0.216 mmol) in Dichloromethane (DCM) (2 mL) was stirred at room temperature. 2,4-Dichloro-3-fluorobenzoyl chloride (36.0 mg, 0.158 mmol) in DCM (0.5 ml) was added and stirring continued at room temperature. After 30 mins, 2 drops MeOH were added followed by sat. NaHCO3 solution (3 ml) and ethyl acetate (30 ml). The product was extracted into the ethyl acetate which was dried (Na2SO4) and concentrated. The product was purified by high pH MDAP to give desired product as a white solid after evaporation of the fractions.

Workup

  1. stirringstirring
  2. customcontinued at room temperature
  3. extractionThe product was extracted into the ethyl acetate which
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product was purified by high pH

Sources & evidence

ORD record
ord-162ec80458744b79b3a7b2321e1143af
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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